So about a year ago I had a roommate that I had always been attracted to but was always to nervous to ask him if he was into guys. One day in casual conversation it finally came up that he was always curious about being with a guy but he was still in the closet. I told him that I would be willing to let him try out gay asshole if he wanted to and he said well maybe, and asked if I would ever tell anyone and I said of course not he said okay well I have one requirement and it is the first time I want you just to be ass up on your bed and blindfolded. I was like okay that’s fine whatever will make you comfortable. So I went to my room undressed myself and just put on my sleep mask and put myself ass up on the bed with a bottle of lube and a condom beside me. I yelled for him that I was ready. He comes in and I hear him release his belt and unzip his pants. I feel him grab my ass and spread it, he then pours some lube on my ass hole and slides two fingers in me a few times. Then he takes a second to do what I guessed at the time was put on the condom and lube up his penis. Then I feel the head of his penis slide its way in, he wasn’t very large which explain the insecurity about me seeing, he was maybe 5 inches but was thick in his own right. He immediately started moaning when he was inside me which turned me on very much so. I said yeah fuck me with that big dick, which I guess already sent him over the edge bc he thirsted his hips up against my ass cheeks and spasmed around inside me and I felt huge amounts of cum splattering the inside of my ass this was when I realized he never used the condom. I was like “did you not use the condom” to which is profusely apologized for. I was like it’s fine haha as I felt his massive load leaking out of my ass onto my bed. This was the beginning of a free use agreement. You see the thing is he was very smart and his parents had loads of money so, in exchange for free food and tutoring for my classes I let him use my asshole every night for the rest of the semester. He would come in with his 5 inch punisher out I would spread my legs and he would dump his hot seed into my ever so inviting ass. His only request was that I not fuck anyone before fucking him for the day. So it worked out well 🙂
